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992-04-1

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992-04-1 Usage

Chemical Properties

white to off-tan powder

Uses

Hexaphenylbenzene was used to prepare the fluorescent nanorods used for the detection of trinitrotoulene (TNT).

Application

Hexaphenylbenzene can be used as a starting material to synthesize:1,2,3,4,5,6-Hexacyclohexylcyclohexane by Pd/C catalyzed hydrogenation reaction.Stable hexatrityl cations and porous organic polymers for applications in catalysis and gas storage.Hexa-peri-hexabenzocoronene via one-pot substitution and oxidative cyclodehydrogenation reaction in the presence of t-BuCl/FeCl3.as a structural unit for the synthesis of polymers of intrinsic microporosity.

Synthesis

Hexaphenylbenzene has been prepared by heating tetraphenylcyclopentadienone and diphenylacetylene without solvent and by trimerization of diphenylacetylene with bis-(benzonitrile)-palladium chloride and other catalysts. The reaction proceeds via a Diels-Alder reaction to give the hexaphenyldienone, which then eliminates carbon monoxide.Multi-Step Synthesis of hexaphenylbenzene from benzilProcedure: Add 0.8 g of tetraphenylcyclopentadienone, 0.8 g of diphenylacetylene (synthesized by you in CH 2270 lab last semester), and 4 g of benzophenone to a 25 mL round-bottom flask. Place a magnetic stir bar in the flask. Make sure no material lodges on the neck or walls of the flask. Attach the condenser to the round-bottom flask. Do not attach the hoses. The condenser will be used as an “air condenser” for this experiment. Heat the reaction mixture VERY HIGH with the sand bath on the hot plate/stirrer. Benzophenone is your solvent and its boiling point is over 300 °C! Heat the reaction mixture to reflux. Carbon monoxide is evolved, the purple color begins to fade in 15-20 minutes, and the color changes to a reddish brown in 25-30 minutes. When no further lightening in color is observed (after about 45 minutes), the heat is removed and 1 mL of diphenyl ether is added to prevent subsequent solidification of the benzophenone. The crystals that separate are brought into solution by reheating and the solution is let stand for crystallization at room temperature. The product is collected and washed free of brown solvent with toluene to give colorless plates.

Check Digit Verification of cas no

The CAS Registry Mumber 992-04-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,9 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 992-04:
(5*9)+(4*9)+(3*2)+(2*0)+(1*4)=91
91 % 10 = 1
So 992-04-1 is a valid CAS Registry Number.
InChI:InChI=1/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H

992-04-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • TCI America

  • (H1412)  Hexaphenylbenzene  

  • 992-04-1

  • 1g

  • 630.00CNY

  • Detail
  • TCI America

  • (H1412)  Hexaphenylbenzene  

  • 992-04-1

  • 5g

  • 2,250.00CNY

  • Detail
  • Alfa Aesar

  • (L00446)  Hexaphenylbenzene, 98+%   

  • 992-04-1

  • 1g

  • 677.0CNY

  • Detail
  • Alfa Aesar

  • (L00446)  Hexaphenylbenzene, 98+%   

  • 992-04-1

  • 5g

  • 2873.0CNY

  • Detail
  • Aldrich

  • (149454)  Hexaphenylbenzene  98%

  • 992-04-1

  • 149454-1G

  • 843.57CNY

  • Detail

992-04-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Hexaphenylbenzene

1.2 Other means of identification

Product number -
Other names 1,2,3,4,5,6-hexakis-phenylbenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:992-04-1 SDS

992-04-1Relevant articles and documents

Synthesis and fluorescence of 3,4,6,7,8,9-hexaphenyl-1H-benzo[g]isochromen-1-one

Loginov, Dmitry A.,Molotkov, Alexander P.,Shepel', Nikolay E.

, p. 67 - 70 (2018)

Highly step- and atom-economic synthetic route to 3,4,6,7,8,9-hexaphenyl-1H-benzo[g]isochromen-1-one (1) based on the rhodium catalyzed reaction of terephthalic acid with diphenylacetylene was developed. The best catalytic system for this reaction is [CpRhI2]n/Cu(OAc)2. Compound 1 shows fluorescent properties with a strong Stokes shift.

Quasilinear 3d-metal(i) complexes [KM(N(Dipp)SiR3)2] (M = Cr-Co) - structural diversity, solution state behaviour and reactivity

Bontemps, Sébastien,Duhayon, Carine,Müller, Igor,Sabo-Etienne, Sylviane,Weller, Ruth,Werncke, C. Gunnar

, p. 4890 - 4903 (2021)

The synthesis and characterization of neutral quasilinear 3d-metal(i) complexes of chromium to cobalt of the type [KM(N(Dipp)SiMe3)2] (Dipp = 2,6-di-iso-propylphenyl) are reported. In solid state these metal(i) complexes either occur as isolated molecules (Co) or are part of a potassium ion linked 1D-coordination polymer (Cr-Fe). In solution the potassium cation is either ligated within the ligand sphere of the metal silylamide or is separated from the complex depending on the solvent. For iron, we showcase that it is possible to use sodium or lithium metal for the reduction of the metal(ii) precursor. However, in these cases the resulting iron(i) complexes can only be isolated upon cation separation using an appropriate crown-ether. Further, the neutral metal(i) complexes are used to introduce NBu4+as an organic cation in the case of cobalt and iron. The impact of the intramolecular cation complexation was further demonstrated upon reaction with diphenyl acetylene which leads to bond formation processes and redox disproportionation instead of η2-alkyne complex formation.

Deactivation of the cobalt catalyst for the cyclotrimerization of acetylenes in ionic liquids: Solvent effects on the mechanism and thermal and pressure activation parameters

Aviles, Teresa,Jansat, Susanna,Martinez, Manuel,Montilla, Francisco,Rodriguez, Carlos

, p. 3919 - 3922 (2011)

The deactivation reaction of the [CoCp(1,4-σ-C4[Ph] 4)PPh3] catalyst for the cyclotrimerization of acetylenes has been kinetico-mechanistically studied under different temperature, pressure, and solvent conditions. The results indicate a dramatic change in mechanism from conventional to ionic liquid solvents due to the polarity of the medium.

Case Study of N-iPr versus N-Mes Substituted NHC Ligands in Nickel Chemistry: The Coordination and Cyclotrimerization of Alkynes at [Ni(NHC)2]

Tendera, Lukas,Helm, Moritz,Krahfuss, Mirjam J.,Kuntze-Fechner, Maximilian W.,Radius, Udo

supporting information, p. 17849 - 17861 (2021/11/17)

A case study on the effect of the employment of two different NHC ligands in complexes [Ni(NHC)2] (NHC=iPr2ImMe 1Me, Mes2Im 2) and their behavior towards alkynes is reported. The reaction of a mixture of [Ni2(iPr2ImMe)4(μ-(η2 : η2)-COD)] B/ [Ni(iPr2ImMe)2(η4-COD)] B’ or [Ni(Mes2Im)2] 2, respectively, with alkynes afforded complexes [Ni(NHC)2(η2-alkyne)] (NHC=iPr2ImMe: alkyne=MeC≡CMe 3, H7C3C≡CC3H7 4, PhC≡CPh 5, MeOOCC≡CCOOMe 6, Me3SiC≡CSiMe3 7, PhC≡CMe 8, HC≡CC3H7 9, HC≡CPh 10, HC≡C(p-Tol) 11, HC≡C(4-tBu-C6H4) 12, HC≡CCOOMe 13; NHC=Mes2Im: alkyne=MeC≡CMe 14, MeOOCC≡CCOOMe 15, PhC≡CMe 16, HC≡C(4-tBu-C6H4) 17, HC≡CCOOMe 18). Unusual rearrangement products 11 a and 12 a were identified for the complexes of the terminal alkynes HC≡C(p-Tol) and HC≡C(4-tBu-C6H4), 11 and 12, which were formed by addition of a C?H bond of one of the NHC N-iPr methyl groups to the C≡C triple bond of the coordinated alkyne. Complex 2 catalyzes the cyclotrimerization of 2-butyne, 4-octyne, diphenylacetylene, dimethyl acetylendicarboxylate, 1-pentyne, phenylacetylene and methyl propiolate at ambient conditions, whereas 1Me is not a good catalyst. The reaction of 2 with 2-butyne was monitored in some detail, which led to a mechanistic proposal for the cyclotrimerization at [Ni(NHC)2]. DFT calculations reveal that the differences between 1Me and 2 for alkyne cyclotrimerization lie in the energy profile of the initiation steps, which is very shallow for 2, and each step is associated with only a moderate energy change. The higher stability of 3 compared to 14 is attributed to a better electron transfer from the NHC to the metal to the alkyne ligand for the N-alkyl substituted NHC, to enhanced Ni-alkyne backbonding due to a smaller CNHC?Ni?CNHC bite angle, and to less steric repulsion of the smaller NHC iPr2ImMe.

Three-Coordinate Iron(0) Complexes with N-Heterocyclic Carbene and Vinyltrimethylsilane Ligation: Synthesis, Characterization, and Ligand Substitution Reactions

Cheng, Jun,Chen, Qi,Leng, Xuebing,Ye, Shengfa,Deng, Liang

, p. 13129 - 13141 (2019/10/11)

Low-coordinate iron(0) species are implicated as intermediates in a range of iron-catalyzed organic transformations. Isolable iron(0) complexes with coordination numbers of less than four, however, are rarely known. In continuing with our interests in three-coordinate iron(0) complexes with N-heterocyclic carbene (NHC) and alkene ligation, we report herein the synthesis and ligand substitution reactivity of three-coordinate iron(0) complexes featuring monodentate alkene ligands, [(NHC)Fe(η2-vtms)2] (vtms = vinyltrimethylsilane, NHC = 1,3-bis(2′,6′-diisopropylphenyl)-imidazol-2-ylidene (IPr), 1; 1,3-bis(2′,6′-diisopropylphenyl)-4,5-tetramethylene-imidazol-2-ylidene (cyIPr), 2; 1,3-bis(2′,6′-diisopropylphenyl)-4,5,6,7-tetrahydro-1,3-diazepin-2-ylidene (7-IPr), 3). Complexes 1-3 were synthesized from the one-pot reactions of ferrous dihalides with the N-(2,6-diisopropylphenyl)-substituted NHC ligands, vtms, and KC8. Reactivity study of 1 revealed its facile ligand substitution reactions with terminal aryl alkynes, ketones, isocyanides, and CO, by which iron(0) complexes [(IPr)Fe(η2-HCCAr)] (Ar = Ph, 5; p-CH3C6H4, 6; 3,5-(CF3)2C6H3, 7), [(IPr)Fe(η2-OCPh2)2] (8), [(IPr)Fe(CNR)4] (R = 2,6-Me2C6H3, 9; But, 10), and (IPr)Fe(CO)4 (11) were prepared in good yields. These iron(0) complexes have been characterized by 1H NMR, solution magnetic susceptibility measurement, single-crystal X-ray diffraction study, 57Fe M?ssbauer spectroscopy, and elemental analysis. Characterization data and computational studies suggest S = 1 ground-spin states for three-coordinate iron(0) complexes 1-3 and 5-8 and S = 0 ground states for 9-11. Theoretical studies on the three-coordinate complexes 1, 6, and 8 indicated pronounced metal-to-ligand backdonation from occupied Fe 3d orbitals to the π* orbitals of the C= C, C=C, and C= O moieties of the πligands. In addition, 1 proved an effective precatalyst for the cyclotrimerization reaction of alkynes.

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